Methanol → N4-(3-ethynylphenyl)quinazoline-4,7-diamine

HRID 1869073Notes

Reaction equation

HRID 1869073 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([N+:21]([O-])=O)=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)#[CH:3].CO.C(Cl)(Cl)Cl.P([O-])(O)O.[Na+]>O1CCCC1.[Pd].O>[NH2:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:2]#[CH:3])[CH:5]=3)=[N:12][CH:13]=[N:14]2)=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 18925068HCID 18925068, compoundHCID 23701735Sodium dihydrogen phosphite

Product 1

HCID 16045588N4-(3-ethynylphenyl)quinazoline-4,7-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The title product of example 12 (1.039 g, 3.18 mmol) was dissolved in 50 mL of tetrahydrofuran, 10 mL of methanol and 5 mL of chloroform at 50° C. Sodium dihydrogen phosphite (NaH2PO2, 3.822 g, 36 mmol) and 10% palladium on carbon (0.19 g) were added followed by dropwise addition of 10 mL of water. When 3 mL of water had been added the mixture became noticeably more homogeneous. After 1 hour the mixture was filtered through Celite. The Celite was washed thoroughly with methanol and chloroform. The combined organic solutions were vacuum evaporated to a residue which was triturated with water, 3% aqueous sodium bicarbonate and filtered. The solid title product was washed with water then diethyl ether and dried in vacuo, 1.054 gm (127%, wet). A portion of the above product was recrystallized from a minimum amount of hot ethanol and water to give, after removal of a small first crop of impure material, pure title product, (43%), mp 180° C. (dec).

Workup

  1. customat 50° C
  2. filtrationAfter 1 hour the mixture was filtered through Celite
  3. washThe Celite was washed thoroughly with methanol and chloroform
  4. customevaporated to a residue which
  5. customwas triturated with water, 3% aqueous sodium bicarbonate
  6. filtrationfiltered
  7. washThe solid title product was washed with water
  8. dry with materialdiethyl ether and dried in vacuo, 1.054 gm (127%, wet)
  9. customA portion of the above product was recrystallized from a minimum amount of hot ethanol and water
  10. customto give
  11. customafter removal of a small first crop of impure material, pure title product, (43%), mp 180° C. (dec)

Sources & evidence

ORD record
ord-5481c0a93abf49a6a173afab2e699d9f
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Reaction notes

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